Loving Someone Who is Self-Employed

I’ve been self-employed for most of the last decade. I’ve gone through seasons of over-working, under-working and everything in between. I’ve been busy and poor. I’ve been thrilled to pursue the life of an entrepreneur and ready to call it quits. My relationship to self- employment has seen many different faces. But, the one complication that has remained throughout the experience has been trying to explain it to the people in my life. Some have understood it more than others and a lot of times anything they didn’t understand it’s because I haven’t communicated it to them well. But, the more I work with other self-employed individuals, the more I see that we’re all facing the same complications in communicating our lives to the people who love us the most. So, today, I thought I’d share just a few things to help you understand and show love to the entrepreneur in your life.

1. Respect their work hours.Yes, we technically make our own hours. Yes, we should have more flexibility. However, we still have to work. It’s almost every single day that someone invites me to do something during my work hours and I’m still working through the guilt in telling people ‘no.’ Many people don’t understand that being self-employed doesn’t mean that we can just pop out for a drink in the middle of the afternoon. At times it can, but, often it means that we are working long days and fitting things in where we can. If you know your self-employed loved one’s work hours, I highly encourage you to not invite them out during that time. Feeling guilty for doing your job is a truly awful feeling.

2. Understand the unique stress involved with self-employment.
Can you remember finals week in school? Maybe you had 2 tests and a paper to write and you felt like the entire world depended on you getting a good grade. That’s our entire life. Except instead of grades it’s our livelihoods and the livelihoods of our families and our employees and our clients. It can be intense. Many self-employed people may need very specific things to manage that high of a level of stress and responsibility. I require an odd balance of routine, play, introspection and alone time. Everyone is different so just ask your person what they need and do your best to be understanding of why they may need that when you may not.

3. Time is extremely valuable.At most times of my self-employed life, time is more valuable than money. Know that the amount of downtime that they have to offer is likely very low and that it’s being divided up between their friends and family and hopefully themselves. Don’t take it personally if you aren’t seeing them as often as you would like. It’s also not uncommon for entrepreneurs to have workaholic tendencies and I’m not saying that’s the best way. But, if you want your loved one to work less, please please please don’t try to make them feel guilty or tell them that they are wrong. When you are in the thick of working too much it feels like you have no other options. The best way to help your self- employed loved one find balance is to encourage them to think about themselves and not to guilt them into spending time with you. The more time they have for themselves the more time they will have for you in the long run.

4. Support is the quickest way to our heart.Being self-employed is a high-risk lifestyle. One that we’ve all likely had to come to grips with in our own ways. I would venture to say that support is the number one thing needed by a self-employed individual. A few ways to support your self-employed love one may be:

– Ask about their day –
It’s not unlikely for someone who is self-employed to live the life of several people in one day and we do it alone for the most part. There are days that I play the role of accountant, marketer, photographer, counselor, writer, brainstormer, and graphic designer in a single day and no one ever really knows about it. That’s an oddly lonely feeling. Asking your loved one questions about what they do in their day and genuinely showing interest in the work they do is a great way to show them you care.

– Show interest in their work –
It’s unlikely that your loved one became self-employed in a profession that they hate or have zero passion for whatsoever. (I mean it happens, but, it’s rare) They chose this profession for a reason, because they enjoy it. Showing genuine interest in their work can mean the world.

– Believe in them –
They’ve already run through all the ways that they could fail in their mind. I promise you. They’ve thought about the risk, they’ve analyzed how they may not be qualified and I guarantee that they feel like an absolute fraud by even saying their dreams out loud. The very last thing that they need is to be told all of the reasons you’re worried that it won’t work. Seriously, don’t do this! If you don’t believe that they can do it, just keep your mouth shut. If you do believe that they can do it, choose the share your support and belief instead of your doubts. Trust me on this one.

– Accept that risk is a part of their reality –
To build on the last point, risk is a given part of the self-employed lifestyle. Everything you do that is new or different is a risk. It’s a daily reality for the self-employed and therefore a daily reality for anyone in relation to someone who is self-employed. The sooner you can accept this truth and find a way to be at ease with it, the better for you and them.

– Hold back the unsolicited advice –
When you are self-employed you are constantly making decisions, changing habits/systems/routines, and moving in one way or another. Your entire life is spent analyzing these decisions, challenges and moves. It’s safe to assume that your self-employed loved one has thought through it all, asked people advice whose opinions they are ready for and analyzed the options. Unless they come to you directly asking for advice, please don’t offer it up. There’s no way to know everything that is happening with them behind the scenes and unsolicited advice can easily be the wrong advice or it could make them feel isolated from you. As a loved one you aren’t a business mentor and that’s totally OK! You aren’t their loved one for your ability to give great business advice, you’re their loved one because you love them, you believe in them and your support them. Know your role in their life and be OK with that.

– Respect that they’re working hard –
Just because they get to choose the timing of their work and just because they may sit behind a computer in a crowded coffee shop to do it and just because they may enjoy what they do, it doesn’t make it any less work. It doesn’t invalidate their stress and it doesn’t mean everything is great all the time. It’s insulting to act as if they’re ‘living the good life.’ and just taking it easy all the time. We all work very hard for the ability to have flexibility in our schedules and most of us don’t even take advantage of that ability. WE ARE WORKING REAL JOBS EVERYONE. We’re not playing pretend over here.

5. Inspiration is important.When your work depends on you staying motivated everyday, inspiration becomes part of your job. You have to put yourself in the position to feel excited to be at work everyday. This is particularly important if you’re in a creative field. It’s nearly impossible to feel creative if you’ve only looked at your own work and a computer screen for the last 8 weeks. It’s important for the creatively self- employed to seek inspiration by going on hikes, taking themselves to the movies, reading a great book or whatever it is that makes them see the world just a bit differently and spurs ideas inside of them. If you can respect that it will make them feel seen and understood and likely loved.

As we all know, I can only write from my experience. Your loved one could disagree with a lot of this and may have a completely different set of needs. But, I encourage you to use this as a starting point for a conversation with them about how you can show up for them in their life a little differently. This is not to say that you should cater your life to the needs of your partner, but, I am writing this with the belief that we all want to love each other better and this may be a start for you to love your self-employed dear one a little bit better.

Post navigation

Sarajane Case is a business coach for female entrepreneurs with high achieving personality types. She works with them to increase productivity, develop systems and eradicate work habits that are no longer serving them through coaching, writing and speaking.

12 comments

Absolutely love this post. Very open and vulnerable to the reality of a self-employed lifestyle. Because it’s not just some way to not work for someone and have more “free time” as people might often think. It is an entire lifestyle that embodies everything you so beautifully wrote. Love it!

Your words complete resonate with me, Sarajane. In fact- if I had written an article on this topic, the points would almost be identical. Thank you for sharing your experiences, they certainly rang true to this Entrepreneur.

“Time is more valuable than money.”
Yes! Yes! Yes! I’ve stopped trying to do DIY hacks & fauxing up projects. You either pay money to do it right, with the correct materials; or you pay with time to do it cheaply with mediocre results. Either way you pay.

I absolutely love this. I am going to share this with my husband in hopes that he’ll understand my choice to be self-employed a little better. It is so hard to put into words how I feel but you nailed it. Thank you!